Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Polymers (Basel). 2024 Jul 24;16(15):2113. doi: 10.3390/polym16152113.

Bio-Based Epoxy Vitrimers with Excellent Properties of Self-Healing, 
Recyclability, and Welding.

Xia J(1)(2), Li S(1)(2), Gao R(1), Zhang Y(1), Wang L(1), Ye Y(1), Cao C(2), Xue 
H(1).

Author information:
(1)Fujian Engineering and Research Center of New Chinese Lacquer Materials, 
Fujian Key Laboratory of Functional Marine Sensing Materials, Minjiang 
University, Fuzhou 350108, China.
(2)College of Environmental and Resource Sciences, Fujian Normal University, 
Fuzhou 350108, China.

The development of more recyclable materials is a key requirement for a 
transition towards a more circular economy. Thanks to exchange reactions, 
vitrimer, an attractive alternative for recyclable materials, is an innovative 
class of polymers that is able to change its topology without decreasing its 
connectivity. In this work, a bisphenol compound (VP) was prepared from 
saturated cardanol, i.e., 3-pentadecylphenol and vanillyl alcohol. Then, VP was 
epoxidized to obtain epoxide (VPGE). Finally, VPGE and citric acid (CA) were 
polymerized in the presence of catalyst TBD to prepare a fully bio-based 
vitrimer based on transesterification. The results from differential scanning 
calorimetry (DSC) showed that the VPGE/CA system could be crosslinked at around 
163 °C. The cardanol-derived vitrimers had good network rearrangement 
properties. Meanwhile, because of the dynamic structural elements in the 
network, the material was endowed with excellent self-healing, welding, and 
recyclability.

DOI: 10.3390/polym16152113
PMCID: PMC11314141
PMID: 39125140

Conflict of interest statement: The authors declare no conflicts of interest.


2. Polymers (Basel). 2024 Jul 4;16(13):1915. doi: 10.3390/polym16131915.

3-Pentadecylphenol (PDP) as a Novel Compatibilizer for Simultaneous Toughened 
and Reinforced PA10,12 Composites.

Jin Y(1)(2)(3), Zhang Q(4), Zhai X(1), Teng H(1), Du Y(1), Lu J(1), Farzana 
S(5), Lee PC(5), Zhang R(4), Luo F(1)(2).

Author information:
(1)State Key Laboratory of High-Efficiency Utilization of Coal and Green 
Chemical Engineering, Ningxia University, Yinchuan 750021, China.
(2)School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 
750021, China.
(3)Chuanghe New Material Technology Jiangsu Co., Ltd., Yangzhou 225000, China.
(4)Key Laboratory of Photovoltaic Materials, School of Materials and New Energy, 
Ningxia University, Yinchuan 750021, China.
(5)Multifunctional Composites Manufacturing Laboratory (MCML), Department of 
Mechanical and Industrial Engineering, University of Toronto, Toronto, ON M5S 
3G8, Canada.

The utilization of polyamide 10,12 (PA10,12) composites in various industries 
has been limited constrained by their inherent low toughness, making it a 
challenge to achieve a balance between toughness and structural integrity 
through conventional elastomer addition strategies. Herein, we introduce a 
straightforward method for the concurrent toughening and reinforcement of 
PA10,12 composites. This is accomplished by blending polyolefin elastomer (POE) 
and 3-pentadecylphenol (PDP) with the PA10,12 matrix. The incorporation of 5 wt% 
PDP effectively blurred the PA10,12/POE interface due to PDP's role as a 
compatibilizer. This phenomenon is attributed to the formation of intermolecular 
hydrogen bonds, as evidenced by Fourier Transform Infrared Spectroscopy (FTIR) 
analysis. Further investigation, using differential scanning calorimetry (DSC), 
elucidated the crystallization thermodynamics and kinetics of the resulting 
binary PA10,12/POE and ternary PA10,12/POE/PDP composites. Notably, the 
crystallization temperature (Tc) was observed to decrease from 163.1 °C in the 
binary composite to 161.5 °C upon the addition of PDP. Increasing the PDP 
content to 10% led to a further reduction in Tc to 159.5 °C due to PDP's 
capacity to slow down crystallization. Consequently, the ternary composite of 
PA10,12/POE/PDP (92/3/5 wt%) demonstrated a synergistic improvement in 
mechanical properties, with an elongation at break of 579% and a notch impact 
strength of 61.54 kJ/m2. This represents an approximately eightfold increase 
over the impact strength of unmodified PA10,12. Therefore, our work provides the 
potential of PDP as a compatibilizer to develop nylon composites with enhanced 
stiffness and toughness.

DOI: 10.3390/polym16131915
PMCID: PMC11243882
PMID: 39000770

Conflict of interest statement: Author Yuwei Jin was employed by the company 
Chuanghe New Material Technology Jiangsu Co., Ltd. The remaining authors declare 
that the research was conducted in the absence of any commercial or financial 
relationships that could be construed as a potential conflict of interest.


3. Mol Pharm. 2024 Jul 1;21(7):3540-3552. doi: 10.1021/acs.molpharmaceut.4c00235.
 Epub 2024 Jun 20.

Complexation Mechanisms of Aqueous Amylose: Molecular Dynamics Study Using 
3-Pentadecylphenol.

Skrdla PJ, Coscia BJ, Gavartin J, Browning A, Shelley J, Sanders JM.

Molecular dynamics (MD) simulations of linear amylose fragments containing 10 to 
40 glucose units were used to study the complexation of the prototypical 
compound, 3-pentadecylphenol (PDP)─a natural product with surfactant-like 
properties─in aqueous solution. The amylose-PDP binding leverages mainly 
hydrophobic interactions together with excluded volume effects. It was found 
that while the most stable complexes contained PDP inside the helical structure 
of the amylose in the expected guest-host (inclusion) complexation manner, at 
higher temperatures, the commonly observed PDP-amylose complexes often involved 
more nonspecific interactions than inclusion complexation. In the case where a 
stoichiometric excess of PDP was added to the simulation box, self-aggregation 
of the small molecule precluded its ability to enter the internal helical part 
of the oligosaccharide, and as a result, inclusion complexation became 
ineffective. MD simulation trajectories were analyzed preliminarily using 
cluster analysis (CA), followed by more rigorous solvent accessible surface area 
(SASA) determination over the temperature range spanning from 277 to 433 K. It 
was found that using the SASA of PDP corrected for its intrinsic conformational 
changes, together with a generic hidden Markov model (HMM), an adequate 
quantification of the different types of PDP-amylose aggregates was obtained to 
allow further analysis. The enthalpy change associated with the guest-host 
binding equilibrium constant (Kgh) in aqueous solution was estimated to be -75 
kJ/mol, which is about twice as high as one might expect based on experimentally 
measured values of similar complexes in the solid state where the (unsolvated) 
helical structure of amylose remains rigid. On the other hand, the nonspecific 
binding (Kns) enthalpy change associated with PDP-amylose interactions in the 
same solution environment was found to be about half of the inclusion 
complexation value.

DOI: 10.1021/acs.molpharmaceut.4c00235
PMID: 38900044 [Indexed for MEDLINE]


4. ACS Omega. 2021 Jul 8;6(28):18235-18247. doi: 10.1021/acsomega.1c02112. 
eCollection 2021 Jul 20.

Confined Crystallization and Melting Behaviors of 3-Pentadecylphenol in Anodic 
Alumina Oxide Nanopores.

Liu Y(1), Wu Y(1), Yao J(1), Yin J(1), Lu J(1), Mao J(1), Yao M(1)(2), Luo F(1).

Author information:
(1)State Key Laboratory of High-Efficiency Coal Utilization and Green Chemical 
Engineering, Ningxia University, 489 Helanshan West Road, Yinchuan 750021, 
China.
(2)Ningxia Baofeng Energy Group, Yinchuan 750001, China.

To explore the effects of end groups on the confined crystallization of an alkyl 
chain, 3-pentadecylphenol (PDP) was infiltrated into the anodic aluminum oxide 
template (AAO) to investigate the melting and crystallization behaviors of PDP 
in a nanoconfined environment. Wide-angle X-ray diffraction (WAXD) found that 
the solid-solid phase transition of PDP occurred under confined conditions, and 
the absence of the (00L) reflections indicated that the stacking of the end 
groups of the alkyl chain layered structure was seriously disturbed. Thermal 
analysis (TG) showed that the thermal stability of the confined samples 
decreased due to the confinement effect, and the introduction of end groups made 
the confinement effect more obvious. Differential scanning calorimeter (DSC) 
results well reflected the space-time equivalence in the PDP crystallization 
processes, i.e., the solid-solid phase transition can be achieved by reducing 
the cooling rate or confining PDP in the nanometer space. Compared with C15, the 
introduction of the end groups with a phenol ring led to the disappearance of 
the solid-solid phase transition of an alkyl chain at high cooling rates. In the 
confined environment, the introduction of the end groups with a phenol ring 
caused the melting double peaks of the alkyl chain to become a single melting 
peak, and it also caused the disappearance of the surface freezing monolayer for 
alkyl chains. Through the analysis of crystallinity, it was found that AAO-PDP 
was more sensitive to AAO pore size changes than AAO-C15, the X c of AAO-PDP had 
a good linear relationship with the pore size d, but the X c of the AAO-C15 had 
a nonlinear relationship with the pore size d. Attenuated total reflection 
(ATR)-IR proved that in the confined environment, the order of the alkyl chain 
decreased and the degree of chain distortion increased.

© 2021 The Authors. Published by American Chemical Society.

DOI: 10.1021/acsomega.1c02112
PMCID: PMC8296606
PMID: 34308054

Conflict of interest statement: The authors declare no competing financial 
interest.


5. ACS Macro Lett. 2020 Jul 21;9(7):1060-1066. doi: 10.1021/acsmacrolett.0c00434.
 Epub 2020 Jul 7.

NMR Studies of Block Copolymer-Based Supramolecules in Solution.

Chang BS(1), Ma L(1), He M(1), Xu T(1)(2).

Author information:
(1)Department of Materials Science and Engineering, University of California, 
Berkeley, Berkeley, California 94720, United States.
(2)Materials Science Division, Lawrence Berkeley National Laboratory, Berkeley, 
California 94720, United States.

Hierarchical assemblies from block copolymer (BCP)-based supramolecules have 
shown immense potential as programmable materials owing to their versatility for 
incorporating functional molecules and provide access to arrays of hierarchical 
structures. However, there remains a knowledge gap on the formation of the 
supramolecule in solution. Here, we applied NMR techniques to investigate the 
solution-phase behavior of the most studied supramolecular systems, 
polystyrene-block-poly(4-vinylpyridine)(3-pentadecylphenol) (PS-b-P4VP(PDP)r). 
The results show that the supramolecule likely adopts a coil-comb conformation, 
despite the small molecule's (PDP) rapid exchange between the bonded and free 
states. The exchange rate (>104 s-1) exceeds the NMR time scale at the frequency 
of interest. The supramolecules form under dilute conditions (∼2 vol %) and are 
attributed to the enthalpic gain of the hydrogen bonding between the PDP and 
4VP. As the solute concentration increases (>10 vol %), the supramolecule forms 
micelle-like aggregates with PDP accumulated within the comb-block's pervaded 
volume based on analysis of the apparent molecular weight, viscosity, and chain 
dynamics. This work sheds light on the long-standing question regarding the 
evolution of the constituents in the BCP-based supramolecule in solution and 
provides valuable guidance toward their solution-based processing and 
morphological control.

DOI: 10.1021/acsmacrolett.0c00434
PMID: 35648616